The present invention relates to novel 5-thiocarbamoyl-1,3,4-oxadiazoles which are active as insecticides.
The cyclization of thio- and dithiocarbazic acid ester derivatives which are acylated in position 3 by the radical of a carboxyic, sulfonic, carbamic, phosphoric, thiophosphoric or thiophosphonic acid with phosgene to give compounds of the formula: ##STR2## where y is O or S, Acyl is --COC.sub.6 H.sub.5, --SO.sub.2 C.sub.6 H.sub.5, CO.sub.2 C.sub.2 H.sub.5, CON(CH.sub.3).sub.2 or ##STR3## is disclosed by Rufenacht in Helvetica Chimica Acta 56, 162-175 (1973). The compounds where Acyl is phosphoryl or thiophosphoryl ##STR4## are disclosed as having an "insecticidal, acaricidal, and nematicidal effect"; however, the compounds where X and O are disclosed as unstable.
Rufenacht, supra, also discloses the preparation of compounds of the formulae: ##STR5## The compounds of formula (B) are disclosed as "having an insecticidal and acaricidal effect" but also as "not stable enough under the conditions of practical pesticide use".
U.S. Pat. No. 3,661,926 issued to Van den Bos et al. discloses 2-oxo-3-dialkoxyphosphoro-5-alkyl (or cycloalkyl of 5 to 7 carbons)-1,3,4-oxadiazolines as insecticidal.
U.S. Pat. No. 3,523,951 issued to Rufenacht teaches derivatives of 1,3,4-thiadiazole as possessing insecticidal activity.
My commonly assigned patent application, "Insecticidal 2-Oxo-3-Dialkoxyphosphoro-5-Cyclopropyl-1,3,4-Oxadiazoline, Ser. No. 343,088, filed Jan. 27, 1982, now U.S. Pat. No. 4,426,379 discloses compounds of the formula: ##STR6## wherein R is hydrogen, lower alkyl or lower alkoxy; R.sup.1 and R.sup.2 are independently lower alkyl; and Y is either oxygen or sulfur.
My commonly assigned U.S. patent application, "Insecticidal N-Carbamoyl-Oxadiazonin-5-Ones and Thiones" Ser. No. 514,073 filed July 15, 1983, discloses insecticidal compounds of the formula: ##STR7## wherein X is oxygen or sulfur; R.sup.1 and R.sup.2 are independently lower alkyl having from 1 to 4 carbon atoms; and R.sup.3 is lower alkyl having from 1 to 6 carbon atoms, lower cycloalkyl having from 3 to 6 carbon atoms optionally substituted with methyl or ethyl, lower alkoxyalkyl having up to a total of 8 carbon atoms or lower alkylthioalkyl having up to a total of 8 carbon atoms.